Mixed tertiary butyl ethers



Patented May 11, 1937 TES UNITED ST PATENT OFFICE MIXED TERTIARY BUTYL ETHERS No Drawing. Original application February 9,

1935, Serial No. 5,854. Divided and this application June 20, 1936, Serial No. 86,336

3 Claims.

This invention relates to mixed tertiary butyl ethers of the general formula R-O-R, wherein R represents the tertiary butyl radical and- OR' represents a branched chain alkoxy 5 radical wherein R. is the alkyl radical of isobutyl alcohol or secondary butyl alcohol.

We are aware that certain elementary mixed ethers have been prepared by various methods but to our knowledge no one has prepared the i0 subaltern genera and species which we claim to constitute our invention.

In our United States Patent 1,968,601, dated July 31, 1934, we have described a process for the production of mixed tertiary ethers which comprises reacting a tertiary-base olefine (an olefine capable of forming a tertiary alcohol by hydration) with an alcohol in the presence of a condensing catalyst such as sulphuric acid.

Now we have discovered that when tertiary butylene (isobutlyene) is reacted with secondary butyl alcohol or isobutyl alcohol, the aliphatic mixed tertiary butyl ethers obtained are valuable compounds which may be used alone, in admixture with each other, or mixed with other sub- 5 stances, as diluting agents, for solutions of various lacquers and varnishes, for example, for solutions of nitrocellulose in ethyl acetate, as solvents and as extracting agents for organic substances such as carboxylic acids, alkaloids, essential oils, essences and the like. The mixed tertiary butyl ethers of this invention form azeotropes with water, which azeotropes contain relatively large amounts of water. This watercarrying property of the ethers makes them particularly suitable water-removing agents in the dehydration of aqueous mixture of organic compounds as alcohols, aldehydes, ketones, aliphatic carboxylic acids and the like.

The novel aliphatic mixed tertiary butyl ethers may be prepared in the manner set out in the following illustrative examples.

EXAMPLE I Tertiary butyl isobutyl ether About 320 gm. of isobutyl alcohol were re-.

temperature of C. for about 1 hour. The mixture was then cooled, poured into dilute caustic and distilled, an azeotrope containing the tertiary butyl isobutyl ether being collected at 825 C. to 83.0" C. This distillate was extracted with an equal volume of dilute sulphuric acid (2 volumes of H20 to 1 volume of H2804), and the upper layer dried with K2003 and distilled. The pure ether was collected at ll3.8 C., some binary isobutyl alcohol-mixed ether azeotrope first 10 coming over at 102 C. A yield of at least gm. of the pure ether was obtained.

EXAMPLE II Tertiary butyl secondary butyl ether 15 About 250 gm. of secondary butyl alcohol, 270 gm. of isobutylene and 18 gm. of sulphuric acid were reacted at a temperature of about '7 5 C. for 1.5 hours. The mixture was then poured into dilute caustic and distilled. The ternary azeotrope (mixed ether-secondary butyl alcohol-water) boiling at 82 C. to 83 C. was collected and treated as in the preparation of tertiary butyl isobutyl ether. The mixed ether obtained boils r at a temperature of 114 C. to 115 C. A yield of at least 75 gm. of the pure ether was obtained.

The foregoing description has been made rather detailed for clearness of understanding only, and no unnecessary limitations should be understood therefrom, but the appended claims should be construed as broadly as possible in View of the prior art.

This application is a division of our application Serial No. 5,854, filed February 9, 1935.

We claim as our invention:

1. The mixed tertiary ether of the formula RO-B, wherein R represents the tertiary butyl radical and -OR' represents a branched chain alkoxy radical wherein R is the alkyl radical of a butyl alcohol of the class consisting of secondary butyl alcohol and isobutyl alcohol.

2. The mixed ether: tertiary butyl isobutyl ether.

3. The mixed ether: tertiary butyl secondary r butyl ether.

THEODORE EVANS. KARL R. EDLUND. 

